(Z)-2-buten-1-yl fluoroacetate | 98064-42-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-buten-1-yl fluoroacetate
• 英文别名: cis-2-butenyl fluoroacetate；Fluoro-acetic acid (Z)-but-2-enyl ester；[(Z)-but-2-enyl] 2-fluoroacetate
• CAS: 98064-42-7
• 化学式: C₆H₉FO₂
• 分子量: 132.135
• InChiKey: FATLZSWRJIOQDV-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-buten-1-yl fluoroacetate 在 三甲基氯硅烷 、 碘 、 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 (3R,4S,5S)-3-Fluoro-5-iodomethyl-4-methyl-dihydro-furan-2-one
  参考文献：
  名称：

  Ester enolate Claisen rearrangements of allyl .alpha.-fluoroacetates and .alpha.-fluoropropanoates

  摘要：

  The ester enolate Claisen rearrangement of allyl alpha-fluoroacetates 1 forms 2-fluoroalkenoic acids 2 in good to excellent yield with good internal asymmetric induction. This selectivity was unexpected as stereoselective deprotonation of fluoroacetates is not normally possible. The selective formation of the required alpha-fluoro silyl ketene acetal 3 was found to result from the stereoselective rearrangement of the allyl alpha-fluoro-alpha-silylacetate isomer. Although silyl ketene acetals derived from alpha-fluoropropanoates 7 also rearranged, control of internal asymmetric induction was not possible.

  DOI：

  10.1021/jo00001a065
• 作为产物：
  描述：

  顺式-2-丁烯-1-醇 、 氟代乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(Z)-2-buten-1-yl fluoroacetate
  参考文献：
  名称：

  Ester enolate Claisen rearrangements of allyl .alpha.-fluoroacetates and .alpha.-fluoropropanoates

  摘要：

  The ester enolate Claisen rearrangement of allyl alpha-fluoroacetates 1 forms 2-fluoroalkenoic acids 2 in good to excellent yield with good internal asymmetric induction. This selectivity was unexpected as stereoselective deprotonation of fluoroacetates is not normally possible. The selective formation of the required alpha-fluoro silyl ketene acetal 3 was found to result from the stereoselective rearrangement of the allyl alpha-fluoro-alpha-silylacetate isomer. Although silyl ketene acetals derived from alpha-fluoropropanoates 7 also rearranged, control of internal asymmetric induction was not possible.

  DOI：

  10.1021/jo00001a065

文献信息

• An improved procedure for the ireland-claisen rearrangement of allyl fluoroacetates
  作者：Koichi Araki、John T. Welch

  DOI：10.1016/s0040-4039(00)77586-1

  日期：1993.4

  The Ireland-Claisen rearrangement of allyl flouroacetates was effected by treatment of the starting esters with trialkylsilyltriflates in the presence of tertiary amines. The stereoselective formation of the products was rationalized as resulting from equilibration of the stereochemistry of the silyl ester products under the reaction conditions.

  氟乙酸烯丙酯的爱尔兰-克莱森重排是通过在叔胺存在下用三烷基甲硅烷基三氟甲磺酸酯处理起始酯来实现的。产物的立体选择性形成是合理的，这是由于在反应条件下甲硅烷基酯产物的立体化学平衡所致。
• Facile diastereoselective ester enolate Claisen rearrangements of allyl fluoroacetates
  作者：John T. Welch、Janet S. Samartino

  DOI：10.1021/jo00219a056

  日期：1985.9
• Peptide modification by incorporation of α-trifluoromethyl substituted α-amino acids
  作者：Klaus Burger、Norbert Sewald、Christian Schierlinger、Kerstin Mütze、Liza C. Seymour

  DOI：10.1016/s0022-1139(00)83708-2

  日期：1991.9
• WELCH, JOHN T.;PLUMMER, JANET S.;CHOU, TSO-SHENG, J. ORG. CHEM., 56,(1991) N, C. 353-359
  作者：WELCH, JOHN T.、PLUMMER, JANET S.、CHOU, TSO-SHENG

  DOI：——

  日期：——
• WELCH, J. T.;SAMARTINO, J. S., J. ORG. CHEM., 1985, 50, N 19, 3663-3665
  作者：WELCH, J. T.、SAMARTINO, J. S.

  DOI：——

  日期：——

表征谱图